Dialkylacetal-containing thromboxane B, 1,9-lactone intermediates

ABSTRACT

The present specification provides novel intermediates and novel processes for the synthesis of various side chain and skeletal analogs of Thromboxane B 2  (11β-homo-11a-oxa-PGF 2 α). These analogs are particularly and especially useful as reproductive cycle control agents.

CROSS REFERENCE TO RELATED APPLICATION

The present application is a divisional application of Ser. No. 716,473,filed Aug. 20, 1976, now issued as U.S. Pat. No. 4,070,384; which is acontinuation-in-part of Ser. No. 676,894, filed Apr. 14, 1976, issued asU.S. Pat. No. 4,018,804 on Apr. 19, 1977.

The present invention relates to processes and intermediates forThromboxane B compounds for which the essential material constituting adisclosure therefor is incorporated by reference herein from U.S. Pat.No. 4,020,173, issued Apr. 26, 1977 and U.S. Pat. No. 4,070,384, issuedJan. 24, 1978. One species of the present invention is(8S,9R,12S)-8[(1'S)-3'-oxo-1'-hydroxypropyl]-9,12-dihydroxy-cis-5-trans-10-heptadecadienoicacid, 9,12 diacetate, dimethylacetal, 1,1'-lactone.

I claim:
 1. A thromboxane intermediate of the formula: ##STR1## whereinZ₁ is (1) CIS--CH═CH--CH₂ --(CH₂)_(g) --CH₂ --,(2) cis--CH═CH--CH₂--(CH₂)_(g) --CF₂ --, (3) cis--CH₂ --CH═CH--(CH₂)_(g) --CH₂ --, (4)--(ch₂)₃ --(ch₂)_(g) --CH₂ --, (5) --(ch₂)₃ --(ch₂)_(g) --CF₂ --, (6)--ch₂ --o--ch₂ --(ch₂)_(g) --CH₂ --, ##STR2## WHEREIN G IS ONE, 2, OR 3;WHEREIN Y₁ is trans-CH═CH- or -CH₂ -CH₂ -; wherein M₃ is ##STR3##wherein R₅ is hydrogen or methyl and R₃₁ is a hydroxyhydrogen replacinggroup; wherein L₁ is ##STR4## or a mixture of ##STR5## wherein R₃ and R₄are hydrogen, methyl, or fluoro, being the same or different with theproviso that one of R₃ and R₄ is methyl only when the other is hydrogenor methyl; andWherein R₇ is (1) --(CH₂)_(m) --CH₃, ##STR6## wherein l iszero, one, two, or three, where m is one to 5, inclusive, T is alkyl ofone to 3 carbon atoms, inclusive, alkoxy of one to 3 carbon atoms,inclusive, chloro, fluoro, or trifluoromethyl, and s is one, two, or 3,the various T's being the same or different, with the proviso that notmore than two T's are other than alkyl, with the further proviso that R₇is ##STR7## only when R₃ and R₄ are hydrogen or methyl, being the sameor different; andwherein R₃₃ is alkyl of one to 5 carbon atomsinclusive. 2.(8S,9R,12S)-8[(1'S)-3'-oxo-1'-hydroxypropyl]-9,12-dihydroxy-cis-5-trans-10-heptadecadienoicacid, 9,12-diacetate, dimethylacetal, 1,1'-lactone, a thromboxaneintermediate according to claim 1.